
Family-friendly vacation rentals in Chincoteague Bay
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Top-rated family-friendly rentals in Chincoteague Bay
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Dragonfli Bay House on Chincoteague Island
Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayaking on the bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

Guesthouse at Vessel Farm & Winery, Waterfront
Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

Private cottage and gardens/comfortable queen bed.
Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

Charming Island Home "Sandy Pines"
Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is). The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

Edgewater Escape - Luxury Bayfront Loft with Porch
You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Cozy Barn Loft: Country Views & Central to Beaches
Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

"Jolly"- Houseboat Getaway
#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

Adorable Waterfront Apartment Weekend Getaway
Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Baywatch Upper-Waterfront & Roaming Ponies!
Calender open for super deals on weekly Summer rentals 2026. Beautiful space in and out! Vacation efficiency, situated right on the bay with views of Assateague across the way, Chincoteague ponies are on premises. Coastal charm at its finest, there are 2 queen bedrooms and livingroom/breakfast room, all with a view. No full kitchen. Microwave, toaster, small fridge, stocked Keurig coffee and tea station and shared outdoor cooking area, sink and bbq grill.

Secluded Waterfront 15mi to Beach•Kayaks•Fast WiFi
Casa Blue Heron is a 2,254 ft² (209 m²) custom home offering stunning water views, a firepit, and serene seclusion at our 3-bedroom waterfront sanctuary by Chincoteague Bay and near Assateague, Berlin, Ocean City, Snow Hill and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature... Wish I had booked an extra day!" Add us to your wish list by clicking the❤️in the upper-right corner.

Bayfront Modern Retreat • Dock, Kayaks, Views
Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginia’s Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.

Ayers Creek Carriage House
Our beautiful carriage house is located on 5 pristine acres along, scenic Ayers Creek, offering year round beauty. Only minutes from Assateague Island, Berlin, and Ocean City. Serene with abundant wildlife. Ideal oasis for outdoor enthusiasts. Worcester County Maryland Rental License #1324
Popular amenities for Chincoteague Bay family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

Peace Point - Waterfront, Secluded, Home w/hot tub

Romantic Saltbox Bungalow! HOT TUB! Bay Sunsets!

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Tiny house w/ Pool on water near Beaches / turf

Hot Tub | Mini Golf | Arcade | Gym — Coastal Quad

Modern Creekside Escape: HotTub-Lux Shower-FirePit
Family- and pet-friendly home rentals

Private romantic pet friendly waterfront cottage

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Ocean City Townhome by Beach Bayside

Historic St.Mary's City at the Lazy Bear Cottage

Nature's retreat @ the Bug-a-Boo. Beaches nearby

Little Red House on a Farm - Quiet Rural Waterview

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Machipongo Glamper
Family-friendly home rentals with a pool

Beach Paradise 202-Downtown Luxury Condo Bay View

Peaceful Haven: nature & charming town

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Bayside community near OCMD great rates

Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi

Waterfront Escape • Pool, Dock & Creek View

Amazing oceanfront view 3 blocks from boardwalk

Ocean Pines marina view condo
Destinations to explore
- Rentals with beach access Chincoteague Bay
- Pet-friendly rentals Chincoteague Bay
- Waterfront rentals Chincoteague Bay
- House rentals Chincoteague Bay
- Fitness-friendly rentals Chincoteague Bay
- Rentals with a fireplace Chincoteague Bay
- Rentals with outdoor seating Chincoteague Bay
- Rentals with pools Chincoteague Bay
- Rentals with a patio Chincoteague Bay
- Rentals with a washer and dryer Chincoteague Bay
- Rentals with a kayak Chincoteague Bay
- Rentals with a fire pit Chincoteague Bay
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